1: 1) KOAc/AcOH 2) aq.NaOH 2: H+ 3: 1) H+ 2) KMnO4/AcOH 3) H+ / acetone 4: pyridine 5: 1) Pb(OAc)4 2) I2 / Irradiation 6: 1) Zn/Hg/HCl 2) aq. NaOH / 1.) reflux, 5 h 2.) reflux, 3 h 7: H+ 8: 350 mg / LiAlH4 / tetrahydrofuran / 3 h / Heating 9: 200 mg / ethylorthoformate/benzoic acid, 3.) alc. KOH / 1.) 70-80 deg C, 1 h 2.) 170 deg C, 4 h 3.) reflux, 8 h View Scheme

1: 1) KOAc/AcOH 2) aq.NaOH 2: H+ 3: 1) H+ 2) KMnO4/AcOH 3) H+ / acetone 4: pyridine 5: 1) Pb(OAc)4 2) I2 / Irradiation 6: 1) Zn/Hg/HCl 2) aq. NaOH / 1.) reflux, 5 h 2.) reflux, 3 h 7: H+ 8: 350 mg / LiAlH4 / tetrahydrofuran / 3 h / Heating 9: 200 mg / ethylorthoformate/benzoic acid, 3.) alc. KOH / 1.) 70-80 deg C, 1 h 2.) 170 deg C, 4 h 3.) reflux, 8 h 10: 100 mg / pyridine / 1 h / Heating View Scheme